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Crystal structure of flucetosulfuron.

Hyunjin Park1, Jineun Kim1, Eunjin Kwon1

  • 1Department of Chemistry (BK21 plus) and Research Institute of Natural Sciences, Gyeongsang National University, Jinju 52828, Republic of Korea.

Acta Crystallographica. Section E, Crystallographic Communications
|December 19, 2017
PubMed
Summary

This study details the crystal structure of a pyrimidinyl-sulfonyl-urea herbicide. Molecular interactions, including hydrogen bonds and pi-pi stacking, form a unique three-dimensional architecture in its crystalline state.

Keywords:
crystal structureflucetosulfuronherbicidespyrimidinyl­sulfonyl­urea herbicide

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Area of Science:

  • Agricultural Chemistry
  • Crystallography
  • Organic Chemistry

Background:

  • Pyrimidinyl-sulfonyl-urea herbicides are vital in modern agriculture.
  • Understanding the molecular structure of herbicides aids in developing more effective and selective agrochemicals.
  • The specific compound 1-[3-({[(4,6-di-meth-oxy-pyrimidin-2-yl)carbamo-yl]amino}-sulfon-yl)pyridin-2-yl]-2-fluoro-propyl 2-meth-oxy-acetate is a notable example.

Purpose of the Study:

  • To elucidate the crystal structure of the title herbicide compound.
  • To investigate the intermolecular interactions governing its solid-state architecture.
  • To provide insights into the structure-activity relationship of pyrimidinyl-sulfonyl-urea herbicides.

Main Methods:

  • Single crystal X-ray diffraction was employed to determine the molecular and crystal structure.
  • Analysis of bond lengths, bond angles, and dihedral angles provided structural details.
  • Intermolecular interactions such as hydrogen bonds and pi-pi stacking were identified and characterized.

Main Results:

  • The dihedral angle between the pyridine and pyrimidine rings was determined to be 86.90(7)°.
  • The crystal structure is stabilized by a network of N/C-H⋯O and C-H⋯F hydrogen bonds, forming a chain along the [020] direction.
  • Weak π-π interactions and additional C-H⋯O hydrogen bonds contribute to the overall three-dimensional architecture.

Conclusions:

  • The detailed crystal structure provides a fundamental understanding of this herbicide's solid-state behavior.
  • The identified intermolecular interactions are crucial for the compound's stability and packing in the crystal lattice.
  • This structural information can guide the design of new herbicides with improved efficacy and environmental profiles.